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First Palladium‐Catalyzed Direct Regioselective C‐5 (Het)Arylation of Mono‐ or Disubstituted Thiazolo[3,2‐ b ][1,2,4]triazoles
Author(s) -
Le Meur Mikaël,
Bourg Stéphane,
Massip Stéphane,
Marchivie Mathieu,
Jarry Christian,
Guillaumet Gérald,
Routier Sylvain
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402193
Subject(s) - regioselectivity , palladium , aryl , catalysis , chemistry , combinatorial chemistry , medicinal chemistry , stereochemistry , organic chemistry , alkyl
Abstract An efficient and convenient method was developed for the formation of polysubstituted thiazolo[3,2‐ b ][1,2,4]triazoles through C‐5 (het)arylation. The direct C–H activation protocol giving access to di‐ and trisubstituted derivatives in excellent yields was optimized. The method is suitable for use with a wide range of (hetero)aryl bromides, and allows access to a collection of C‐5,6 bis(het)aryl derivatives with full regioselectivity. The results are supported by a full description of all final compounds, and X‐ray crystallographic data confirmed that the spectroscopic analyses were interpreted correctly.